# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_230616h1_0m
_database_code_depnum_ccdc_archive 'CCDC 2288402'
loop_
_audit_author_name
_audit_author_address
'dilshat abdukerem'
;Xinjiang University
China
;
_audit_update_record             
;
2023-08-13 deposited with the CCDC.	2024-02-02 downloaded from the CCDC.
;
_audit_creation_date             2023-06-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 O3 S Se'
_chemical_formula_sum            'C21 H18 O3 S Se'
_chemical_formula_weight         429.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.005(4)
_cell_length_b                   11.035(4)
_cell_length_c                   18.194(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.800(7)
_cell_angle_gamma                90
_cell_volume                     1966.2(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3351
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.352
_cell_measurement_theta_min      2.287
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.033
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0924 before and 0.0520 after correction.
The Ratio of minimum to maximum transmission is 0.7635.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             872
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11408
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.928
_diffrn_reflns_theta_min         2.159
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3182
_reflns_number_total             4544
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.547
_refine_diff_density_min         -1.517
_refine_diff_density_rms         0.215
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1795
_refine_ls_R_factor_gt           0.1494
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1075P)²+64.9128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3917
_refine_ls_wR_factor_ref         0.4049
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C18(H18), C20(H20), C21(H21), C11(H11), C3(H3), C13(H13),
 C15(H15), C2(H2), C17(H17), C9(H9), C19(H19), C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.84617(15) 0.40830(14) 0.56286(9) 0.0435(6) Uani 1 1 d . . . . .
S1 S 0.5626(3) 0.2846(3) 0.51438(19) 0.0324(8) Uani 1 1 d . . . . .
O1 O 0.4983(11) 0.3726(9) 0.5558(5) 0.039(2) Uani 1 1 d . . . . .
O3 O 0.7429(12) 0.2124(9) 0.4072(7) 0.052(3) Uani 1 1 d . . . . .
O2 O 0.6222(10) 0.1778(9) 0.5544(7) 0.047(3) Uani 1 1 d . . . . .
C1 C 0.4494(13) 0.2394(11) 0.4328(7) 0.028(3) Uani 1 1 d . . . . .
C4 C 0.6886(13) 0.3729(11) 0.4798(8) 0.034(3) Uani 1 1 d . . . . .
H4 H 0.646026 0.450752 0.462787 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7868(14) 0.4040(13) 0.3596(8) 0.038(3) Uani 1 1 d . . . . .
C8 C 0.2502(15) 0.1721(15) 0.3075(8) 0.043(3) Uani 1 1 d . . . . .
C10 C 0.7390(13) 0.3179(12) 0.4140(8) 0.033(3) Uani 1 1 d . . . . .
C12 C 0.4285(15) 0.1202(12) 0.4135(8) 0.039(3) Uani 1 1 d . . . . .
H12 H 0.481677 0.061205 0.442167 0.047 Uiso 1 1 calc R U . . .
C14 C 0.9550(12) 0.2657(12) 0.5601(8) 0.036(3) Uani 1 1 d . . . . .
C16 C 0.2695(18) 0.2936(16) 0.3265(9) 0.054(4) Uani 1 1 d . . . . .
H16 H 0.217445 0.352069 0.296796 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3291(16) 0.0850(14) 0.3515(9) 0.047(4) Uani 1 1 d . . . . .
H18 H 0.315751 0.003334 0.339731 0.056 Uiso 1 1 calc R U . . .
C20 C 1.0467(18) 0.2627(16) 0.5139(11) 0.056(4) Uani 1 1 d . . . . .
H20 H 1.049187 0.323534 0.478810 0.067 Uiso 1 1 calc R U . . .
C21 C 0.3659(17) 0.3296(13) 0.3896(9) 0.049(4) Uani 1 1 d . . . . .
H21 H 0.375494 0.410862 0.403132 0.058 Uiso 1 1 calc R U . . .
C11 C 0.7546(17) 0.5296(15) 0.3563(10) 0.052(4) Uani 1 1 d . . . . .
H11 H 0.704824 0.563375 0.389064 0.062 Uiso 1 1 calc R U . . .
C3 C 0.8637(18) 0.3566(18) 0.3088(10) 0.055(4) Uani 1 1 d . . . . .
H3 H 0.886160 0.274720 0.309929 0.066 Uiso 1 1 calc R U . . .
C13 C 0.798(2) 0.6001(17) 0.3038(11) 0.060(5) Uani 1 1 d . . . . .
H13 H 0.776140 0.681995 0.300789 0.073 Uiso 1 1 calc R U . . .
C7 C 0.141(2) 0.134(2) 0.2400(11) 0.074(6) Uani 1 1 d . . . . .
H7A H 0.053748 0.133094 0.253740 0.111 Uiso 1 1 calc R U . . .
H7B H 0.162179 0.055148 0.223710 0.111 Uiso 1 1 calc R U . . .
H7C H 0.139685 0.191350 0.199873 0.111 Uiso 1 1 calc R U . . .
C15 C 1.1365(19) 0.165(2) 0.5215(16) 0.082(7) Uani 1 1 d . . . . .
H15 H 1.202461 0.163559 0.492162 0.098 Uiso 1 1 calc R U . . .
C2 C 1.133(2) 0.0724(19) 0.5686(15) 0.083(7) Uani 1 1 d . . . . .
H2 H 1.190750 0.006141 0.569081 0.099 Uiso 1 1 calc R U . . .
C17 C 0.952(2) 0.1754(19) 0.6138(14) 0.074(6) Uani 1 1 d . . . . .
H17 H 0.892515 0.181052 0.646632 0.089 Uiso 1 1 calc R U . . .
C9 C 0.873(2) 0.554(2) 0.2560(11) 0.071(6) Uani 1 1 d . . . . .
H9 H 0.903300 0.604114 0.221776 0.086 Uiso 1 1 calc R U . . .
C19 C 0.904(2) 0.432(2) 0.2584(11) 0.074(6) Uani 1 1 d . . . . .
H19 H 0.954116 0.400897 0.224795 0.089 Uiso 1 1 calc R U . . .
C5 C 1.041(2) 0.077(2) 0.6175(18) 0.096(9) Uani 1 1 d . . . . .
H5 H 1.038924 0.014823 0.651889 0.116 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se01 C4 1.987(13) . ?
Se01 C14 1.920(13) . ?
S1 O1 1.457(10) . ?
S1 O2 1.448(10) . ?
S1 C1 1.745(13) . ?
S1 C4 1.805(14) . ?
O3 C10 1.172(16) . ?
C1 C12 1.367(18) . ?
C1 C21 1.428(18) . ?
C4 H4 0.9800 . ?
C4 C10 1.52(2) . ?
C6 C10 1.52(2) . ?
C6 C11 1.42(2) . ?
C6 C3 1.42(2) . ?
C8 C16 1.39(2) . ?
C8 C18 1.39(2) . ?
C8 C7 1.52(2) . ?
C12 H12 0.9300 . ?
C12 C18 1.40(2) . ?
C14 C20 1.37(2) . ?
C14 C17 1.40(2) . ?
C16 H16 0.9300 . ?
C16 C21 1.40(2) . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C20 C15 1.39(2) . ?
C21 H21 0.9300 . ?
C11 H11 0.9300 . ?
C11 C13 1.37(2) . ?
C3 H3 0.9300 . ?
C3 C19 1.36(3) . ?
C13 H13 0.9300 . ?
C13 C9 1.36(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C2 1.34(3) . ?
C2 H2 0.9300 . ?
C2 C5 1.41(4) . ?
C17 H17 0.9300 . ?
C17 C5 1.40(3) . ?
C9 H9 0.9300 . ?
C9 C19 1.38(3) . ?
C19 H19 0.9300 . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 Se01 C4 100.7(5) . . ?
O1 S1 C1 110.6(6) . . ?
O1 S1 C4 103.5(6) . . ?
O2 S1 O1 117.5(7) . . ?
O2 S1 C1 108.9(6) . . ?
O2 S1 C4 111.7(6) . . ?
C1 S1 C4 103.7(6) . . ?
C12 C1 S1 122.2(10) . . ?
C12 C1 C21 119.2(13) . . ?
C21 C1 S1 118.3(10) . . ?
Se01 C4 H4 107.1 . . ?
S1 C4 Se01 110.1(7) . . ?
S1 C4 H4 107.1 . . ?
C10 C4 Se01 109.8(9) . . ?
C10 C4 S1 115.3(9) . . ?
C10 C4 H4 107.1 . . ?
C11 C6 C10 122.7(14) . . ?
C3 C6 C10 118.6(14) . . ?
C3 C6 C11 118.7(16) . . ?
C16 C8 C7 120.3(16) . . ?
C18 C8 C16 119.4(14) . . ?
C18 C8 C7 120.3(16) . . ?
O3 C10 C4 120.2(13) . . ?
O3 C10 C6 122.1(14) . . ?
C6 C10 C4 117.6(12) . . ?
C1 C12 H12 119.3 . . ?
C1 C12 C18 121.4(14) . . ?
C18 C12 H12 119.3 . . ?
C20 C14 Se01 119.5(12) . . ?
C20 C14 C17 121.6(15) . . ?
C17 C14 Se01 118.2(13) . . ?
C8 C16 H16 119.4 . . ?
C8 C16 C21 121.1(15) . . ?
C21 C16 H16 119.4 . . ?
C8 C18 C12 120.0(13) . . ?
C8 C18 H18 120.0 . . ?
C12 C18 H18 120.0 . . ?
C14 C20 H20 121.4 . . ?
C14 C20 C15 117.2(19) . . ?
C15 C20 H20 121.4 . . ?
C1 C21 H21 120.6 . . ?
C16 C21 C1 118.9(14) . . ?
C16 C21 H21 120.6 . . ?
C6 C11 H11 120.6 . . ?
C13 C11 C6 118.8(18) . . ?
C13 C11 H11 120.6 . . ?
C6 C3 H3 120.4 . . ?
C19 C3 C6 119.3(18) . . ?
C19 C3 H3 120.3 . . ?
C11 C13 H13 119.0 . . ?
C9 C13 C11 121.9(19) . . ?
C9 C13 H13 119.0 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C20 C15 H15 118.2 . . ?
C2 C15 C20 124(2) . . ?
C2 C15 H15 118.2 . . ?
C15 C2 H2 120.5 . . ?
C15 C2 C5 119(2) . . ?
C5 C2 H2 120.5 . . ?
C14 C17 H17 120.5 . . ?
C5 C17 C14 119(2) . . ?
C5 C17 H17 120.5 . . ?
C13 C9 H9 120.1 . . ?
C13 C9 C19 119.9(19) . . ?
C19 C9 H9 120.1 . . ?
C3 C19 C9 121(2) . . ?
C3 C19 H19 119.3 . . ?
C9 C19 H19 119.3 . . ?
C2 C5 H5 120.4 . . ?
C17 C5 C2 119(2) . . ?
C17 C5 H5 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se01 C4 C10 O3 94.7(14) . . . . ?
Se01 C4 C10 C6 -83.7(12) . . . . ?
Se01 C14 C20 C15 171.2(14) . . . . ?
Se01 C14 C17 C5 -173.7(18) . . . . ?
S1 C1 C12 C18 174.4(12) . . . . ?
S1 C1 C21 C16 -176.5(14) . . . . ?
S1 C4 C10 O3 -30.3(17) . . . . ?
S1 C4 C10 C6 151.3(9) . . . . ?
O1 S1 C1 C12 -131.7(12) . . . . ?
O1 S1 C1 C21 41.6(14) . . . . ?
O1 S1 C4 Se01 74.8(7) . . . . ?
O1 S1 C4 C10 -160.3(9) . . . . ?
O2 S1 C1 C12 -1.1(15) . . . . ?
O2 S1 C1 C21 172.2(12) . . . . ?
O2 S1 C4 Se01 -52.6(9) . . . . ?
O2 S1 C4 C10 72.3(11) . . . . ?
C1 S1 C4 Se01 -169.6(6) . . . . ?
C1 S1 C4 C10 -44.8(11) . . . . ?
C1 C12 C18 C8 1(2) . . . . ?
C4 S1 C1 C12 117.9(13) . . . . ?
C4 S1 C1 C21 -68.8(13) . . . . ?
C6 C11 C13 C9 -1(3) . . . . ?
C6 C3 C19 C9 0(3) . . . . ?
C8 C16 C21 C1 3(3) . . . . ?
C10 C6 C11 C13 -177.9(14) . . . . ?
C10 C6 C3 C19 178.3(16) . . . . ?
C12 C1 C21 C16 -3(2) . . . . ?
C14 C20 C15 C2 3(3) . . . . ?
C14 C17 C5 C2 2(4) . . . . ?
C16 C8 C18 C12 -1(2) . . . . ?
C18 C8 C16 C21 -1(3) . . . . ?
C20 C14 C17 C5 -3(3) . . . . ?
C20 C15 C2 C5 -5(4) . . . . ?
C21 C1 C12 C18 1(2) . . . . ?
C11 C6 C10 O3 165.1(14) . . . . ?
C11 C6 C10 C4 -16.5(19) . . . . ?
C11 C6 C3 C19 0(2) . . . . ?
C11 C13 C9 C19 2(3) . . . . ?
C3 C6 C10 O3 -13(2) . . . . ?
C3 C6 C10 C4 165.2(13) . . . . ?
C3 C6 C11 C13 0(2) . . . . ?
C13 C9 C19 C3 -1(3) . . . . ?
C7 C8 C16 C21 178.1(18) . . . . ?
C7 C8 C18 C12 -179.9(16) . . . . ?
C15 C2 C5 C17 2(4) . . . . ?
C17 C14 C20 C15 1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
